It was a wet December night at Stadio San Nicola in 1999 as FC Bari played host to Inter Milan in Serie A. Inter were already clear favourites prior to the game as circumstances conspired against the home side; both of Bari’s regular forwards were sidelined through injury. Opportunities were given to two young and unproven forwards in Nigerian, Hugo Enyinnaya, and a local teenager by the name of Antonio Cassano. The latter was about to write his name into Bari’s history books as he took his first steps into what would turn out to be a notorious career in professional football.

In the 87th minute, with the score tied at 1-1, a long ball from Simone Perrotta found Cassano in space in the left hand channel. With a mesmeric first touch, he instantly brought the ball under his spell, moving effortlessly into the open field in front of him. His skilful dribbling left Laurent Blanc and Christian Panucci in his wake as he cut inside the two defenders and drove the ball into the penalty area before calmly finishing past the goalkeeper to claim a famous 2-1 victory for i Galletti. 

As the ball hit the back of the net, Cassano erupted in celebration. Exuding passion and pride, he jumped over the advertising boards and galloped across the running track, arms held aloft to celebrate with the home supporters. It was a moment that would come to define Cassano’s professional career, flashes of brilliance fuelled by pure emotion.

When he first emerged as a youngster with Bari, Cassano had already fought through adversity just to make it as a professional footballer. He was raised by his mother, who held down two jobs to support the family in one of Bari’s poorest neighbourhoods, Old Town. His father had abandoned them when Cassano was just a baby and football proved to be a saviour for the young Italian who became schooled in the art of street football.

Rarely attending school and occasional run-ins with the law were an early indicator of the volatile character that would make Cassano infamous on and off the pitch. Had his ability with a football not been spotted by one of Bari’s scouts, his life may have taken a very different path, as he detailed in his 2010 autobiography, Dico Tutto (I’ll Tell You Everything):

“If it wasn’t for that game against Inter I would have become a thief or worse; either way, a delinquent. A lot of people that I know have become involved in that life. That game my talent shone, and it took me away from a future of potential shit.”

Cassano made his Serie A debut at 17 and became known as Il Gioiello di Bari Vecchia – or ‘The Jewel of Old Bari’. He was the clubs most valuable asset, a young, home-grown player blessed with vision, technique and an eye for goal. A move to a bigger club in Italy beckoned.

Fabio Capello was the man to take a chance on Cassano when he signed the 19-year-old for AS Roma in 2001 for a fee in the region of €30 million. This made Cassano the most expensive teenage footballer at the time.

His impact in the Italian capital wasn’t instant as he only managed 6 goals in 30 appearances during his first season. His second and third seasons in the Eternal City proved much more fruitful as he began to show the flashes of brilliance which had previously put world-class defenders such as Blanc and Panucci to the sword.

Cassano developed a formidable partnership with club captain Francesco Totti. The pair’s passing, off-the-ball movement and general link up play bordered on clairvoyant and ensnared the home supporters inside the Stadio Olimpico. The Italian double act propelled Roma into the runners-up spot behind AC Milan in a memorable campaign in 2003-04 as they scored 34 league goals between them.

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Despite their prolific form with Roma, Cassano and Totti’s blossoming partnership was not given the opportunity to flourish on the international stage. Although Giovanni Trapattoni had named both forwards in his Italy squad, only Totti would start the first game at the European Championships in the summer of 2004.

This wasn’t all that surprising considering the wealth of attacking options afforded to Trapattoni at the time, with Alessandro Del Piero, Christian Vieri and Totti all to fit into the starting line-up. This left little room for a 21-year-old Cassano who would make up the bench with fellow forwards Marco Di Vaio and Bernardo Corradi.

Had it not been for Totti’s moment of madness in Italy’s opening game of the tournament against Denmark, Cassano may never have got his opportunity to shine at Euro 2004. UEFA handed Totti a three match, retrospective ban for spitting at Danish midfielder, Christian Poulsen, meaning he would miss the rest of Italy’s campaign.

Cassano was given a starting place by Trapattoni in the next two matches. Despite scoring in the 1-1 draw against Sweden and in the 2-1 win over Bulgaria where he also earned the man of the match award, he couldn’t prevent Italy’s elimination from what was a disappointing tournament for a side brimming with world-class players.

Cassano’s career was on an upward trajectory, in-form at club level and breaking into the Italian senior side, the stage was set for him to develop into a truly world-class forward for club and country.

Thanks to his own character, the opportunity to become an Italian hero was beginning to slip through his fingers. Volatile and temperamental, Cassano became notorious for clashing with his manager or tipping over the emotional edge on the pitch. No more so than in the second leg of the 2003 Coppa Italia final against AC Milan where he received a red card and caused controversy by flashing the ‘sign of the horns’ at the referee as he left the pitch.

A string of four managers had come and gone since Capello’s departure from Roma in 2004 and Luciano Spalletti picked up where his predecessors left off, instantly finding himself on the receiving end of Cassano’s latest outburst: “You’re not coaching those useless players you had at Udinese. This isn’t your house, it’s my house.”

His lack of respect for his new manager was not surprising considering he had already endured a fractious relationship with one of the most formidable, disciplined and authoritarian coaches in the game. Allegedly, Capello and Cassano told each other to “fuck off” on numerous occasions whilst together at Roma.

In fact, the only manager Cassano claimed he never fought with was Eugenio Fascetti, the man who brought him through into the first team at Bari.

With his Roma contract set to expire in the summer of 2006, Cassano was seeking a more lucrative deal with i Giallorossi. The dispute continued for the first half of the 2005-06 season with Cassano spending most of his time on the bench. The feud with Spalletti persisted meaning Cassano would continue to be left out of the side and even Roma’s chief officer, Rosella Sensi, criticised the player for his conduct. After Cassano had spoken publicly about compromising on his salary demands, Sensi said: “He is a liar and our lawyers are evaluating his comments. It is not true that he made two steps back. He has never done that and in fact, we made a step forward in the negotiations, so he really can’t be allowed to come out with certain things.

“We have been very patient but he undervalued the importance of our offer. Cassano has had all the time that he wanted and his response is only lies.”

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To exacerbate his troubles, the Totti-Cassano axis had been broken beyond repair. The two had struck up one of the most formidable and aesthetic partnerships in Serie A but the relationship had begun to sour after the pair had appeared on a television show hosted by Maria De Filippi. Cassano was unhappy that the Roma captain had taken home 80 percent of the appearance fee; a seemingly trivial matter but one which the unpredictable Cassano took to heart.

The extended conflict between the player, the club and his teammates curtailed any chance of a new contract and effectively sealed his exit. Roma decided to cut their losses before losing Cassano for free in the summer and a meagre €5 million fee saw the Italian depart for Real Madrid in January 2006. The Galácticos beckoned.

A dream move for any footballer, Cassano was given the opportunity to play alongside legends such as Zinedine Zidane, Raúl and David Beckham. However, his short time at Los Blancos was unsurprisingly fraught with controversy. He was only the second Italian to play for the Spanish giants after Panucci and, despite scoring three minutes into his debut in the Copa del Rey against Real Betis, his playing time quickly became limited.

He embraced the playboy lifestyle in the Spanish capital, gaining excessive amounts of weight and sleeping with numerous women. Food and sex were Cassano’s vices. In his autobiography, the forward claimed he had slept with around 600 or 700 women and that it was easy to get away with his habits in Madrid, even before a match”

“In Madrid I had a friend who was a hotel waiter. His job was to bring me three or four pastries after I had sex. He would bring the pastries up the stairs, I would escort the woman to him and we would make an exchange: he would take the girl and I would take the pastries. Sex and then food, a perfect night.”

Cassano’s penchant for women and food caused his downfall at Madrid who eventually began to fine him for every gram he was overweight, leading to the nickname El Gordito or ‘The Little Fatty’. The rows with Capello and disciplinary action that followed meant Cassano was exiled from the first team. Lack of fitness and form saw any chance of making Marcello Lippi’s Italy squad for the 2006 World Cup disappear as quickly as one of his beloved pastries.

Calciopoli left a dark shadow lingering over Italy and the one chance of redemption rested with the national team in Germany. Cassano’s fitness and discipline meant he missed out on the chance to lift the World Cup trophy with his teammates at the Olympiastadion in Berlin.

Cassano believed he could revive his Madrid career, especially after he was reunited with his old Roma manager, Capello, who was appointed manager at Real in July 2006. Unfortunately, their relationship remained as ill-natured as ever and it seemed Cassano’s days in Spain were numbered.

He openly criticised his manager for omitting him from the team. In his autobiography, Cassano recalled the moment he unleashed a tirade of abuse at Capello in the dressing room before a match against Tarragona, labelling him “ … a piece of shit! You’re more fake than monopoly money!”

Cassano was also captured on video mocking Capello in front of his team-mates. The forward was subsequently fined and banned from training with the squad.

Madrid president at the time, Ramón Calderón, publicly stated that “ … he’s [Cassano] shown a lack of respect. His statements were impertinence.” Cassano’s continued indiscipline and emotional outbursts led Capello to coin the term cassanata, which literally meant ‘doing a Cassano’.

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Disillusioned with life in Spain, Cassano claimed that he would “walk all the way back” to play for Roma again. Comments which were not greeted favourably by Roma chief officer, Sensi.

His genius on the pitch had been completely eclipsed by his temperament and the forward was farmed back to Italy with Sampdoria after a mere two goals in 19 appearances in Spain. While Cassano was still capable of the brilliance required to unlock the most stubborn defence, his own arrogance and explosive personality meant it would be an arduous task to rebuild his career.

Ruined relationships and missed opportunities epitomised Cassano’s time at Real Madrid and his last days at Roma. Sampdoria was a far cry from two of Europe’s biggest clubs, but nevertheless, Cassano joined on a season-long loan deal. This was the opportunity for the struggling Italian to reignite his career.

During his first season with i Blucerchiati, it seemed that Cassano had shaken off the fitness and weight issues which had plagued his time at Madrid as he began to demonstrate the skilful dribbling and technical prowess for which he was renowned. His form had returned and the goals were beginning to flow again but he was never far away from a moment of madness.

Playing on the emotional edge, Cassano broke down in tears after he received a yellow card against Fiorentina. The booking meant a one-match suspension and cruelly, he would not be able to feature in Sampdoria’s next match against his old club, Roma. After remonstrating passionately with the referee and linesman, he slumped to his knees near the touchline, weeping into the turf. Players from both sides eventually offered him some comfort in what was a surreal emotional outburst reminiscent of Paul Gascoigne at Italia 90.

In a match against Torino in March 2008, Cassano exploded yet again, this time in anger rather than despair, after he received a red card late on in the 2-2 draw. His emotions got the better of him as he refused to leave the field, protesting wildly, shouting, swearing and eventually throwing his shirt at the referee. His impetuous actions earned him a five-match ban and a €15,000 fine.

Despite the moments of madness, his form had remained relatively consistent and he eventually joined Sampdoria on a permanent basis, becoming the creative hub and goal threat for the team. Cassano formed a strong partnership with fellow forward, Giampaolo Pazzini which drove i Blucerchiati to Champions League qualification in 2010.

Although all was going well, Cassano again proved to be his own worst enemy. This time he found himself in an argument with Sampdoria’s president, Riccardo Garrone, after refusing to attend an awards presentation night. The situation shared similar characteristics to the row with Totti and Sensi at Roma and added to the growing list of Cassano’s misdemeanours.

With both men as stubborn as one another, Garrone had become so incensed by the forward’s refusal to attend the ceremony that he attempted to have his contract cancelled for gross misconduct. However, the tribunal deliberating the situation ruled that Cassano’s pay should be halved as punishment.

Garrone spoke about his desire to get rid of Cassano in an interview with Tuttosport: “Unfortunately, with what has happened I must maintain this stance. I’m very sorry because if Cassano didn’t have that temper, and if he was not a bit of a funny guy every now and then with no self-control, then he could have been one of the greatest players in the world.”

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Once again, Cassano parted ways with a club with resent in his heart. His form in the 2009-10 season had meant that there was a vast pool of potential suitors and, eventually, AC Milan stumped up the €3.3 million fee to sign the Italian in January 2011.

A 28-year-old Cassano joined an ageing but strong Milan squad whose forward line consisted of Zlatan Ibrahimović, Robinho and Alexander Pato. He struggled to break into the starting 11, only managing seven goals in 33 league appearances over two seasons. However, minutes on the pitch turned out to be the least of his worries during his time with the Rossoneri.

In October 2011, after appearing as a substitute in a 2-3 victory against Roma, Cassano had fallen ill on the Milan team bus travelling from the airport. Complaining of dizziness and struggling to speak coherently, the club doctor convinced Cassano to visit the hospital. It turned out to be more serious than first feared as doctors diagnosed him as having suffered from an ischemic stroke.

Cassano feared for his life, never mind his football career: “We argued for half an hour before I agreed to visit the hospital. And that is when I started to have trouble speaking and thought about seeing my son again.” He was operated on four days later to correct a heart problem that had caused the stroke.

He recalled the fear he felt: “If I am honest I was afraid of dying, in particular during those days before the operation.” He continued to talk about the support he received: “ … the important thing is that I got through it and that everyone, from Real Madrid to Barcelona, from Mourinho to Delneri and even Iniesta phoned me. I know I have the power and the will to return to the pitch.”

Remarkably, Cassano returned to the pitch only five months after his operation, making a substitute appearance in Milan’s 1-2 loss against Fiorentina. Cassano even managed to play his way into Lippi’s Italy squad for Euro 2012, spearheading the attack with Mario Balotelli as Italy finished runners-up in the tournament behind Spain.

Following the sale of several of Milan’s star players – including Ibrahimović, Pato and Thiago Silva – in the summer of 2012, Cassano requested a transfer and crossed the divide to join Inter Milan in a player-plus-cash deal for his former Sampdoria team-mate, Pazzini. He spent one season with Inter, scoring seven goals in 28 league games before he was on the move again.

This time there was no ill-feeling or resentment, it seemed that two, life-changing events had helped to curb his hot-headedness. The marriage to his wife, Carolina Marcialis, in 2010 and the stroke he suffered in October 2011 had really made an impact on the forward and Cassano vowed not to waste his second chance.

Affectionately known as Fantantonio, Cassano is currently a free agent having left Sampdoria in 2017.

Former Real Madrid player and General Manager, Jorge Valdano, was complimentary of Cassano in an interview for Spanish online sports journal, Marca: “(Andrea) Pirlo is the substance of the Italian football team, while Cassano is the imagination. He is a player who at any time of the game has solutions that neither the coach nor the other players can give.”

Described by Gianluca Vialli as a mix of Gianfranco Zola and Paolo Di Canio, Cassano remains a genius with a football at his feet. However, with his genius comes the touch of madness and raw emotion that fuels his performance on the field. People may tell you that Cassano was the greatest Italian player that never was but without his madness, he may not have been the player we know today. Without the madness, maybe the genius would never have been realised at all?

There is a certain romantic attraction to players of Cassano’s ilk and what is for certain, he has led one of the most colourful and inspirational careers. A true rags to riches story of a player who battled adversity and enjoyed life at the top in the most spectacular fashion 

By Jamie Allen. Follow @plymkrprss